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Polybrominated diphenyl ether and synthesizing method thereof

A technology for polybrominated diphenyl ethers and brominated diphenyl ethers, which are applied in the field of polybrominated diphenyl ethers and their synthesis, can solve the problems of difficult bromine substitution reaction, few bromine substitution digits, and no reports on the synthesis of high brominated OH/MeO-PBDEs.

Inactive Publication Date: 2010-11-10
SHANGHAI UNIV
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Problems solved by technology

These two kinds of methods have all used iodized iodized salt, because the iodized salt that can make is all low bromine, and the iodized salt of high bromine is synthesized difficultly.
Therefore, although the method is simple and easy to operate, the number of bromine substitutions on the benzene ring of the final product is very small, and what they synthesized is mainly OH / MeO-PBDEs with 4-6 bromines, and cannot obtain 7-9 bromines. High bromine OH / MeO-PBDEs
In the synthesis of high-bromine OH / MeO-PBDEs, due to the large number of bromine atoms and large steric hindrance on the target molecule, the bromine substitution reaction is difficult during the synthesis process.
Therefore, at present, there are no reports on the synthesis of high-bromine OH / MeO-PBDEs at home and abroad.

Method used

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  • Polybrominated diphenyl ether and synthesizing method thereof
  • Polybrominated diphenyl ether and synthesizing method thereof
  • Polybrominated diphenyl ether and synthesizing method thereof

Examples

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Embodiment 1

[0057] Embodiment one (taking the preparation process of A23 as example):

[0058] a. Taking 2-methoxy-5-aminophenol (1.39g, 10.0mmol) and 5-fluoro-2-nitroaniline (1.39g, 10.0mmol) as raw materials, in N,N-dimethylacetamide (DMAC, 15mL) as solvent and anhydrous Na 2 CO 3 (1.06g, 10.0mmol) was used as a catalyst for Williamson coupling reaction under the reaction conditions of 140°C, and the coupling product 5-(2-methoxy-4-aminophenol hydroxy)-2-nitroaniline A1 could be obtained after 3 hours of reaction. After the reaction solution was cooled, it was extracted with saturated brine and ethyl acetate, and the organic phase was extracted, washed with 1M NaOH (3×30ml), and then washed with distilled water (3×30ml). Column chromatography, the developing solvent is ethyl acetate / n-hexane 1:1, and drained to obtain a dark red solid. Yield: 1.80g, yield 65%; 1 H NMR: δ=8.08(d, J H4 =9.5Hz, 1H,H3), 6.32(dd, J H3，H6 =9.5, 2.5Hz, 1H, H4), 6.10(d, J H4 = 2.5Hz, 1H, H6), 6.86(d, J ...

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Abstract

The invention relates to polybrominated diphenyl ether and a synthesizing method thereof. The polybrominated diphenyl ether has a general formula shown in the specification of the invention, wherein the substituting groups corresponding to R1, R2, R3 and R4 are R1 R2 R3 R4H Br Br BrBr H Br BrBr Br H BrBr Br Br HBr Br Br Br. The invention makes reasonable utilization of the positioning bromination ability of amino and the property of easily being substituted by bromine atom or hydrogen atom, provides possibility for synthesizing various high bromine OH / MeO-PBDEs, and can provide sample support for detecting metabolite of high bromine OH / MeO-PBDEs of bromine 7-9 in the environment.

Description

Technical field: [0001] The invention relates to a polybrominated diphenyl ether and a synthesis method thereof. Background technique: [0002] At present, the synthesis of OH / MeO-PBDEs in the world is mainly carried out by German companies. Marsh's team is working, but they are mainly for the synthesis of low-bromine OH / MeO-PBDEs. Its synthesis method is mainly synthesized by two methods: the first method is prepared by Ullmann coupling reaction between iodide iodide salt and m-methoxyphenol containing two bromines. Another method is to use the product of iodine iodide and 3-hydroxybenzaldehyde Ullmann coupling, further Baeye-Villliger oxidation reaction to convert the aldehyde group into a hydroxyl group, and then carry out bromine substitution according to the ortho- and para-position effect of the hydroxyl group. These two kinds of methods have all used iodized iodized salt, because the iodized salt that can make is all low bromine, and the iodized salt of high bromin...

Claims

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Application Information

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IPC IPC(8): C07C43/29C07C41/01C07C41/22
Inventor 郑柯文冯红涛汪德成刘宏远魏建辉
Owner SHANGHAI UNIV
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